data_GS3
# 
_chem_comp.id                                    GS3 
_chem_comp.name                                  2-fluoro-6-{[2-({2-methoxy-4-[4-(1-methylethyl)piperazin-1-yl]phenyl}amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}benzamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H31 F N8 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-09-24 
_chem_comp.pdbx_modified_date                    2008-12-26 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        518.586 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GS3 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3EKN 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
GS3 C1   C1   C 0 1 N N N -0.116 19.872 20.551 -2.253  3.773  -1.756 C1   GS3 1  
GS3 O1   O1   O 0 1 N N N 1.132  19.669 19.898 -1.364  2.794  -1.213 O1   GS3 2  
GS3 C2   C2   C 0 1 Y N N 2.162  19.955 20.796 -1.923  1.650  -0.736 C2   GS3 3  
GS3 C3   C3   C 0 1 Y N N 1.938  20.089 22.150 -3.295  1.474  -0.790 C3   GS3 4  
GS3 C4   C4   C 0 1 Y N N 2.977  20.393 23.006 -3.864  0.305  -0.303 C4   GS3 5  
GS3 C5   C5   C 0 1 Y N N 4.239  20.537 22.459 -3.057  -0.687 0.238  C5   GS3 6  
GS3 C6   C6   C 0 1 Y N N 4.471  20.387 21.108 -1.687  -0.513 0.293  C6   GS3 7  
GS3 C7   C7   C 0 1 Y N N 3.424  20.098 20.255 -1.115  0.651  -0.198 C7   GS3 8  
GS3 N1   N1   N 0 1 N N N 3.546  19.938 18.854 0.276   0.825  -0.147 N1   GS3 9  
GS3 C8   C8   C 0 1 Y N N 4.596  20.336 18.013 1.112   -0.280 -0.113 C8   GS3 10 
GS3 N2   N2   N 0 1 Y N N 5.563  21.119 18.505 2.414   -0.091 0.056  N2   GS3 11 
GS3 C9   C9   C 0 1 Y N N 6.587  21.497 17.727 3.256   -1.119 0.095  C9   GS3 12 
GS3 N3   N3   N 0 1 N N N 7.638  22.317 18.172 4.614   -0.917 0.272  N3   GS3 13 
GS3 C10  C10  C 0 1 Y N N 7.822  22.810 19.474 5.098   0.361  0.532  C10  GS3 14 
GS3 C11  C11  C 0 1 Y N N 6.766  23.165 20.289 4.274   1.315  1.111  C11  GS3 15 
GS3 C12  C12  C 0 1 Y N N 6.993  23.653 21.557 4.756   2.583  1.369  C12  GS3 16 
GS3 C13  C13  C 0 1 Y N N 8.276  23.799 22.041 6.062   2.915  1.053  C13  GS3 17 
GS3 C14  C14  C 0 1 Y N N 9.338  23.452 21.234 6.899   1.980  0.476  C14  GS3 18 
GS3 F1   F1   F 0 1 N N N 10.618 23.578 21.659 8.173   2.309  0.170  F1   GS3 19 
GS3 C15  C15  C 0 1 Y N N 9.101  22.968 19.966 6.426   0.689  0.214  C15  GS3 20 
GS3 C16  C16  C 0 1 N N N 10.274 22.607 19.156 7.314   -0.316 -0.396 C16  GS3 21 
GS3 O2   O2   O 0 1 N N N 10.376 22.948 17.988 7.373   -0.420 -1.606 O2   GS3 22 
GS3 N4   N4   N 0 1 N N N 11.190 21.869 19.861 8.059   -1.121 0.387  N4   GS3 23 
GS3 C17  C17  C 0 1 Y N N 6.600  21.056 16.415 2.735   -2.415 -0.046 C17  GS3 24 
GS3 C18  C18  C 0 1 Y N N 7.466  21.228 15.305 3.304   -3.762 -0.059 C18  GS3 25 
GS3 C19  C19  C 0 1 Y N N 6.924  20.533 14.252 2.281   -4.614 -0.235 C19  GS3 26 
GS3 N5   N5   N 0 1 Y N N 5.770  19.949 14.684 1.105   -3.913 -0.335 N5   GS3 27 
GS3 C20  C20  C 0 1 Y N N 5.561  20.259 16.001 1.348   -2.572 -0.224 C20  GS3 28 
GS3 N6   N6   N 0 1 Y N N 4.536  19.865 16.757 0.580   -1.484 -0.246 N6   GS3 29 
GS3 N7   N7   N 0 1 N N N 2.747  20.531 24.395 -5.251  0.126  -0.357 N7   GS3 30 
GS3 C21  C21  C 0 1 N N N 3.997  20.454 25.127 -5.637  -1.174 0.208  C21  GS3 31 
GS3 C22  C22  C 0 1 N N N 3.658  20.165 26.566 -7.148  -1.365 0.058  C22  GS3 32 
GS3 N8   N8   N 0 1 N N N 2.842  21.304 27.063 -7.848  -0.268 0.741  N8   GS3 33 
GS3 C23  C23  C 0 1 N N N 1.621  21.586 26.231 -7.462  1.033  0.176  C23  GS3 34 
GS3 C24  C24  C 0 1 N N N 1.985  21.725 24.759 -5.950  1.223  0.326  C24  GS3 35 
GS3 C25  C25  C 0 1 N N N 2.596  21.203 28.541 -9.303  -0.455 0.684  C25  GS3 36 
GS3 C26  C26  C 0 1 N N N 3.910  21.389 29.275 -9.991  0.635  1.509  C26  GS3 37 
GS3 C27  C27  C 0 1 N N N 1.714  22.351 28.962 -9.773  -0.367 -0.769 C27  GS3 38 
GS3 H1   H1   H 0 1 N N N 0.043  19.924 21.638 -1.679  4.634  -2.100 H1   GS3 39 
GS3 H1A  H1A  H 0 1 N N N -0.564 20.813 20.200 -2.799  3.342  -2.596 H1A  GS3 40 
GS3 H1B  H1B  H 0 1 N N N -0.791 19.035 20.319 -2.958  4.090  -0.988 H1B  GS3 41 
GS3 H3   H3   H 0 1 N N N 0.941  19.955 22.544 -3.923  2.246  -1.211 H3   GS3 42 
GS3 H5   H5   H 0 1 N N N 5.068  20.774 23.110 -3.501  -1.596 0.617  H5   GS3 43 
GS3 H6   H6   H 0 1 N N N 5.472  20.496 20.717 -1.061  -1.285 0.715  H6   GS3 44 
GS3 HN1  HN1  H 0 1 N N N 2.780  19.479 18.403 0.654   1.718  -0.136 HN1  GS3 45 
GS3 HN3  HN3  H 0 1 N N N 8.325  22.576 17.492 5.227   -1.666 0.216  HN3  GS3 46 
GS3 H11  H11  H 0 1 N N N 5.753  23.059 19.929 3.253   1.066  1.361  H11  GS3 47 
GS3 H12  H12  H 0 1 N N N 6.154  23.925 22.181 4.109   3.322  1.819  H12  GS3 48 
GS3 H13  H13  H 0 1 N N N 8.446  24.179 23.037 6.428   3.910  1.258  H13  GS3 49 
GS3 HN4  HN4  H 0 1 N N N 10.877 21.720 20.799 8.011   -1.038 1.352  HN4  GS3 50 
GS3 HN4A HN4A H 0 0 N N N 12.053 21.527 19.488 8.643   -1.783 -0.014 HN4A GS3 51 
GS3 H18  H18  H 0 1 N N N 8.382  21.800 15.291 4.346   -4.022 0.051  H18  GS3 52 
GS3 H19  H19  H 0 1 N N N 7.339  20.462 13.257 2.370   -5.688 -0.289 H19  GS3 53 
GS3 HN5  HN5  H 0 1 N N N 5.168  19.380 14.124 0.230   -4.311 -0.464 HN5  GS3 54 
GS3 H21  H21  H 0 1 N N N 4.628  19.652 24.717 -5.115  -1.971 -0.322 H21  GS3 55 
GS3 H21A H21A H 0 0 N N N 4.555  21.398 25.042 -5.370  -1.205 1.265  H21A GS3 56 
GS3 H22  H22  H 0 1 N N N 3.088  19.227 26.642 -7.412  -1.361 -0.999 H22  GS3 57 
GS3 H22A H22A H 0 0 N N N 4.573  20.050 27.166 -7.441  -2.316 0.503  H22A GS3 58 
GS3 H23  H23  H 0 1 N N N 0.910  20.755 26.347 -7.729  1.063  -0.881 H23  GS3 59 
GS3 H23A H23A H 0 0 N N N 1.173  22.531 26.573 -7.983  1.829  0.706  H23A GS3 60 
GS3 H24  H24  H 0 1 N N N 2.591  22.629 24.599 -5.687  1.220  1.383  H24  GS3 61 
GS3 H24A H24A H 0 0 N N N 1.082  21.818 24.138 -5.657  2.174  -0.119 H24A GS3 62 
GS3 H25  H25  H 0 1 N N N 2.140  20.228 28.767 -9.560  -1.434 1.090  H25  GS3 63 
GS3 H26  H26  H 0 1 N N N 4.734  21.434 28.547 -11.071 0.496  1.467  H26  GS3 64 
GS3 H26A H26A H 0 0 N N N 3.878  22.325 29.851 -9.657  0.572  2.545  H26A GS3 65 
GS3 H26B H26B H 0 0 N N N 4.071  20.542 29.959 -9.734  1.613  1.104  H26B GS3 66 
GS3 H27  H27  H 0 1 N N N 1.499  22.274 30.038 -9.283  -1.143 -1.357 H27  GS3 67 
GS3 H27A H27A H 0 0 N N N 2.228  23.302 28.758 -10.853 -0.506 -0.812 H27A GS3 68 
GS3 H27B H27B H 0 0 N N N 0.771  22.315 28.397 -9.516  0.612  -1.175 H27B GS3 69 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
GS3 C1  O1   SING N N 1  
GS3 O1  C2   SING N N 2  
GS3 C2  C3   DOUB N N 3  
GS3 C2  C7   SING N N 4  
GS3 C3  C4   SING N N 5  
GS3 C4  C5   DOUB Y N 6  
GS3 C4  N7   SING Y N 7  
GS3 C5  C6   SING Y N 8  
GS3 C6  C7   DOUB N N 9  
GS3 C7  N1   SING Y N 10 
GS3 N1  C8   SING N N 11 
GS3 C8  N2   DOUB Y N 12 
GS3 C8  N6   SING N N 13 
GS3 N2  C9   SING Y N 14 
GS3 C9  N3   SING N N 15 
GS3 C9  C17  DOUB N N 16 
GS3 N3  C10  SING N N 17 
GS3 C10 C11  DOUB N N 18 
GS3 C10 C15  SING Y N 19 
GS3 C11 C12  SING Y N 20 
GS3 C12 C13  DOUB Y N 21 
GS3 C13 C14  SING N N 22 
GS3 C14 F1   SING Y N 23 
GS3 C14 C15  DOUB N N 24 
GS3 C15 C16  SING N N 25 
GS3 C16 O2   DOUB Y N 26 
GS3 C16 N4   SING Y N 27 
GS3 C17 C18  SING Y N 28 
GS3 C17 C20  SING N N 29 
GS3 C18 C19  DOUB Y N 30 
GS3 C19 N5   SING N N 31 
GS3 N5  C20  SING Y N 32 
GS3 C20 N6   DOUB N N 33 
GS3 N7  C21  SING N N 34 
GS3 N7  C24  SING Y N 35 
GS3 C21 C22  SING N N 36 
GS3 C22 N8   SING N N 37 
GS3 N8  C23  SING N N 38 
GS3 N8  C25  SING N N 39 
GS3 C23 C24  SING N N 40 
GS3 C25 C26  SING Y N 41 
GS3 C25 C27  SING Y N 42 
GS3 C1  H1   SING Y N 43 
GS3 C1  H1A  SING N N 44 
GS3 C1  H1B  SING Y N 45 
GS3 C3  H3   SING N N 46 
GS3 C5  H5   SING Y N 47 
GS3 C6  H6   SING N N 48 
GS3 N1  HN1  SING Y N 49 
GS3 N3  HN3  SING N N 50 
GS3 C11 H11  SING N N 51 
GS3 C12 H12  SING N N 52 
GS3 C13 H13  SING N N 53 
GS3 N4  HN4  SING N N 54 
GS3 N4  HN4A SING N N 55 
GS3 C18 H18  SING N N 56 
GS3 C19 H19  SING N N 57 
GS3 N5  HN5  SING N N 58 
GS3 C21 H21  SING N N 59 
GS3 C21 H21A SING N N 60 
GS3 C22 H22  SING N N 61 
GS3 C22 H22A SING N N 62 
GS3 C23 H23  SING N N 63 
GS3 C23 H23A SING N N 64 
GS3 C24 H24  SING N N 65 
GS3 C24 H24A SING N N 66 
GS3 C25 H25  SING N N 67 
GS3 C26 H26  SING N N 68 
GS3 C26 H26A SING N N 69 
GS3 C26 H26B SING N N 70 
GS3 C27 H27  SING N N 71 
GS3 C27 H27A SING N N 72 
GS3 C27 H27B SING N N 73 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
GS3 SMILES           ACDLabs              10.04 Fc1cccc(c1C(=O)N)Nc3nc(nc2nccc23)Nc5ccc(N4CCN(C(C)C)CC4)cc5OC 
GS3 InChI            InChI                1.02b 
InChI=1/C27H31FN8O2/c1-16(2)35-11-13-36(14-12-35)17-7-8-20(22(15-17)38-3)32-27-33-25-18(9-10-30-25)26(34-27)31-21-6-4-5-19(28)23(21)24(29)37/h4-10,15-16H,11-14H2,1-3H3,(H2,29,37)(H3,30,31,32,33,34)/f/h30-32H,29H2 
GS3 InChIKey         InChI                1.02b HXZDICYKFAOZLE-PQJGUGOOCQ 
GS3 SMILES_CANONICAL CACTVS               3.341 COc1cc(ccc1Nc2nc3[nH]ccc3c(Nc4cccc(F)c4C(N)=O)n2)N5CCN(CC5)C(C)C 
GS3 SMILES           CACTVS               3.341 COc1cc(ccc1Nc2nc3[nH]ccc3c(Nc4cccc(F)c4C(N)=O)n2)N5CCN(CC5)C(C)C 
GS3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)N1CCN(CC1)c2ccc(c(c2)OC)Nc3nc4c(cc[nH]4)c(n3)Nc5cccc(c5C(=O)N)F 
GS3 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)N1CCN(CC1)c2ccc(c(c2)OC)Nc3nc4c(cc[nH]4)c(n3)Nc5cccc(c5C(=O)N)F 
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
GS3 "SYSTEMATIC NAME" ACDLabs              10.04 2-fluoro-6-{[2-({2-methoxy-4-[4-(1-methylethyl)piperazin-1-yl]phenyl}amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}benzamide 
GS3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-fluoro-6-[[2-[[2-methoxy-4-(4-propan-2-ylpiperazin-1-yl)phenyl]amino]-7H-pyrrolo[3,2-e]pyrimidin-4-yl]amino]benzamide     
# 
